I am creating a Generator that can randomly generate two people that exist on the source engine, and have their names display on the screen so people can make fights in Gmod with the two characters and upload them to Youtube.

I have it set so it randomly generates a number, 1 through 5, using "random(1.5)". However, the generation button doesn't work. It stays at "Unset".

What he said, and since you were giving random() a floating-point number ( . = decimal point here, to be clear), it was generating one of those from 0 up to (not including)1.5, therefore making it impossible to match anything but the name for 1, which would still be a long-shot. Feed it an integer, and it acts as Citnarf said.

Also, you could replace all of those events for the different names with something like this: